Episode Transcript
I like trying to ask the question that's on the edge of what's It's askable, because I think I learn about a person beyond just their answer to the question. I learn how do they respond to a situation that's a little uncommon. And as a VC, I'm competing with other VCs, I'm selling money to entrepreneurs, and it is from a marketing perspective important that I stand out. And so asking questions that are different from the questions other people ask is an important fact to me as well. That's intentional. I don't ask questions for the sake of standing out, but it's why when I think of something that might be on the edge of being uncomfortable, I try to find a way to ask it. Hey everyone, it's Antonia with an episode of QuestionAble Strategy and the voice that you just heard was Roy Bahat, who is the head of Bloomberg Beta. Bloomberg Beta is Bloomberg LP, we've heard of it, their investing arm. And so that actually means that Roy is one of the top voices in the world on the future of work technology. He's also an MBA lecturer at UC Berkeley, but really interestingly, he got to start working for New York city mayor, Michael Bloomberg, at the beginning of his career, which is a pretty nontraditional path for a tech VC. So in our conversation, we talk a lot about investing. We talk about the world of tech. We talk about how questions play a role when he's evaluating other companies that he might invest in, but also we get to talk a little bit about his own background and how the political world has influenced him as well as his experience as a founder. I could not imagine having a better guest as my first interview for QuestionAble Strategy. I'm really excited. To share this conversation where we talk about questions that VC asks. So without further ado, here is my conversation with Roy Bahat. Roy, welcome to the QuestionAble Strategy podcast. I'm really excited for our conversation today. Me too. Kicking this off. I think that it is appropriate to tell everybody and yourself. I don't think I've said this to you, but you're actually one of the. Inspirations for this podcast. I remember back in 2021 pitching you the idea for Toucan as an investor, and I remember you asking me the most insightful questions that I really wasn't asked ever from VCs. And that really made an impression on me and made me think about how VCs go about their inquiry. And that's why I'm so excited to learn from you today. Yay! I mean, I kind of feel like you should tell me what works about questions, because I'm on the giving end, not the receiving end. And so, you can instruct me as much as I have any sense of what I did. Well, then why don't we'll, we'll learn from each other, but I want to start with a question that I love asking people, which is who inspired you to be curious? Hmm. I think it's come from a few places, as best as I can tell. I'll say my personality has always been, I'm a little bit maybe sometimes a lot bit insecure about what I don't know. And so curiosity and learning are a way that I address that in myself by just trying to get more knowledgeable and like of all my many identities, and we all have many of them, student is probably the one where I've felt in my life, the most comfortable and where I still feel the most comfortable. And then I would say kind of like early childhood stuff. Being in a Jewish home inspired a lot of it because there's a culture of questioning and a culture of trying to understand and most of the like, elder figures that you read about were themselves mostly in a kind of Socratic process of asking questions and trying to understand things. It's almost like if you had a religion whose heroes are professors, it's kind of always felt like that a little bit to me. Yeah. And then I had a first boss, who was really meaningful for me. He wasn't my first, first boss, but my first like really meaningful boss. And sorry to the people who came before this, you were slightly less meaningful, I'm sure there'll be listening to Yeah, no, they might you might get some hate mail. Ben I learned a lot from you, but it was only three months. So I'll just say my main first boss that I learned a lot from, is Dan Doctoroff, who, before I worked with him, had run a private equity firm for a very long time, had built a nonprofit, when I worked with him, he was, deputy mayor in city government and went on to do a lot of really incredible things. He had a way of doing things where his learning process. To figure out what to do about a project was I'm going to load this a bit. He was an interrogator He would interrogate people about their work. He would interrogate people about their personal lives and While sometimes that was really uncomfortable I learned a lot about what kind of questions actually get you to the heart of the matter really rapidly. And I'll say just by observation, not working as closely, but Mike Bloomberg was the mayor I've heard of him. yeah, right. The couple meetings that I sat in with him when I was in my twenties, it was so different from how I expected a meeting should go. I had been trained that like you come in with a crisp agenda and you get through it and then you finish whatever. And when Mike would meet with somebody, he would often have, I mean, I'm literally not exaggerating, 30 or 45 minutes of personal conversation about what was going on in their lives and what they were thinking about. What was going on with their kids. And then almost all of a sudden out of nowhere, he would ask the one question that was the only one that mattered about the thing at hand and get it done. What that showed me is not so much like you should ramble with people for 45 minutes. But more that. Unlike school where you're studying something. It's like, what are the 30 questions about this thing? I need to answer in life. Often it's identifying the one question that matters. So I think about that a lot. What is the one question on which everything else turns? In your experience, how have you gone about trying to figure out what that one question is in different scenarios? Yeah, trial and error, I mean, I just say as an investor now, I've had a first conversation with a founder, might literally be thousands of times at this point, all doing reasonably similar things from reasonably similar cultures. I mean, hopefully they have lots of diversity, but they're all generally speaking, based in North America. And so a lot of it is just repetition and trial and error. In the beginning, I'm thinking. What's the highest importance thing for me to understand? And sometimes it'll be, a thing totally different from what that person is talking about. I had this conversation the other day with somebody, they're like, we're going to speed this thing up. Our competitors, it currently takes a month. We can do it in a day and we're going to get it so it can happen in minutes. And. My first question was, does that even matter? Is the difference between a day and a month enough for your customers? And then I think, well, what does matter? I mean, are your customers interested in buying this thing? Maybe that's the thing that matters the most. And so it's surprising how quickly you can get to the right question. If really all you're doing is thinking hard about what is the one question that matters, it's not always just one, but what are, what's the short list of the fewest number of things that actually matter? Just thinking back to our conversation, what really struck me was how many questions you actually asked me about my personal background, which no other VCs were asking me. The question that stands out to me that I remember three years later is you asked me how my parents specifically raised me as a kid. Huh. And this is the first conversation that we'd ever had. I even think that this was over audio. I don't even think this was a video call. So I couldn't, stare you in the eyes. And I just got into a whole story about what my childhood was like. And this is at a time when I was having tons of VC calls where they're asking me the same dry questions about product market fit and where I saw the video conferencing industry going in the next couple of years. And then here you were asking me about how my parents raised me. why would you think that that is important? Is a question I've been meaning to ask you for three years. that's amazing and I'm so happy you brought it up because I'm going to speculate because I don't actually remember. I will say it's not a standard question that I have. It's not like I go trying to like dig deep on somebody's personal life. So. My guess is that you said something that gave me a clue that that might be particularly important for you. You might have said something about what one of your parents attitudes was toward the startup or made some other offhand comment. So some of what I'm doing is I'm listening for the clues. of what somebody's telling me is important. and It's not a question I typically ask. And so my hypothesis is you said something that made me guess that that might be the thing. And in a sense, every question is a bet. You're betting on whether it's worth the time to get that knowledge from somebody. And one of the things I think that I do bias toward is if a possible question comes up for me, And I wonder, is it appropriate to ask this question? Which I would say that question is probably borderline appropriate. You know, there's a power dynamic where like, I'm not trying to, you know, if I'd asked you like, what are your childhood traumas? Like that would be inappropriate, right? Probably. But I like trying to ask the question that's on the edge of what's It's askable, because I think I learn about a person beyond just their answer to the question. I learn how do they respond to a situation that's a little uncommon. And as a VC, I'm competing with other VCs, I'm selling money to entrepreneurs, and it is from a marketing perspective important that I stand out. And so asking questions that are different from the questions other people ask is an important fact to me as well. That's intentional. I don't ask questions for the sake of standing out, but it's why when I think of something that might be on the edge of being uncomfortable, I try to find a way to ask it. I'll give you another example from another point in my career. When I was a founder and we were pitching our business, we were very close to a final offer and in the partner meeting with a VC firm and the CEO, she's my former coworker. She was the boss and this firm had had some public trouble around gender discrimination issues. And I was like, I'm going to ask about this. And she's like, Oh my God, please don't, in part because she was, to be honest, kind of indifferent. She was the kind of person, I don't know if she was indifferent, but she acted indifferent. And she's like, I just want to win. And I was like, that's great. I still want to ask. And the way I ask the question is, I said to this VC firm, do you think we should feel as a company run by a woman if we were to work with a venture firm being sued by one of its former partners for gender discrimination? I didn't accuse them of anything. I asked things only based on facts. Nothing was subjective there. And I asked it in terms of advice for us as opposed to an accusation about them. So I found a way that I thought was really appropriate given the setting to ask about a really difficult issue. And by the way, the partner who later led the deal, and I couldn't believe this, Literally said we love backing businesses run by chicks and the woman, the female partner in the room, she was a major reason we wanted to work with the firm. She later left. But I just saw her eyes, grow wide and, That told me that I was learning something about how they work with each other in that moment. And that was a core issue And so finding a way to ask about the core issue not making it a yes or no But like if I thought something was important in your childhood I was guessing at that, but I was finding some way to ask that felt like it was appropriate, but just barely. Absolutely. And It's clear in the fact that I've been thinking about this interaction for three years, not in a, oh, this made me feel uncomfortable way, but in a way where I applaud you for asking me something that I really never got asked about before, but that I was really proud of. That speaks volumes, I think. When that happens, it's great, but I will just say it, it's only risk because it can go badly. And so there are definitely cases where I've asked a question and they did not like it. And I mean, I had a case where I was getting to the core question and a founder literally stood up, walked away from the table, came back a minute later and was like, sir. Good day. I can see this isn't gonna work. And it's like, All right. You know, I asked him to sit down. I was like, I think I've probably offended you. Can we talk about it? And he was like, You VCs, you think you know everything? I was like, I was just asking questions about this thing. But he could tell that the questions were coming from a perspective that I didn't get it. You know, I'd say to people sometimes, I do not understand what you're saying. And literally somebody said to me, I'm offended that you said that. She's like, I'm a great communicator and she has a great communicator, but I didn't understand what she was saying. So sometimes the truth can be really offensive for people, even if it's my truth. My truth was, I didn't understand what she were saying. I'm curious to hear a bit more about these cues What I look for in cues is. The music somebody plays while they're talking, not the text of what they're saying, but the subtext of what they're saying. Okay. Look, if I ask a founder, would you sell this business? If you got an offer tomorrow for X, they're basically all going to say no to the point where I don't even ask that kind of question, but the way they say no would tell me a lot. There's a huge difference between saying no by saying like, what? I wouldn't even consider it versus, Well, I don't even think I would consider it. You know, those are two totally different answers in terms of what they say about the response. So there's music that gets played. There is differences from the norm. So my guess is you said something about one parent that was just unexpected in that context. And so because it's unexpected for me, it's a clue that there might be something there. And the other thing is under the breath comments. We are trained as human beings to pay the most attention to something when somebody wants us to pay attention. So if I slow down right now, and I tell you, I'm about to say something really important. You're trained to believe something important is about to happen. Even though I just said nothing, literally, I just said nothing important. But what I've found is that oftentimes the most important things are the things where someone's like, Oh yeah, that other bot. And then they keep going and it's like, wait, wait, wait, hold on. That's the moment where somebody, and you know, I learned that by just paying attention to myself to when the most important stuff leaks out. I guess that brings us back to a comment that you made at the very, very beginning that I wanted to ask you more about, which is insecurity about what it is that you don't know. How do you turn that insecurity into great questions as opposed to clamming up and maybe avoiding talking about something in a conversation or, changing the subject or getting really quiet? Yeah. I mean, my one word answer is practice. Meaning you have to be intentional about trying, my longer answer is that you can learn these things. And so trying to learn it is a big deal for sure. Recognizing you'll get it wrong. A question I often ask myself is, What, what happens if I get it wrong? Like, what am I afraid of? And sometimes the answer is I'm afraid of something really bad and I want to avoid it. Sometimes it's like, well, I'm afraid this founder might not like me. You know, it's like, I don't know. I don't really care. Like I, I want to be respected by founders. if I say something I think is appropriate and they are bothered, I'd talk to them about it if they, reveal to me that that they're offended and I'd want to get curiosity about it. But you know, if at the end of the day I go to bed and I offended a founder by asking a professionally worded appropriate question, not my fucking problem. I recently was in a situation where I was among a pool of what I can only assume are very, very qualified people trying to get this one opportunity. And I decided to go for broke and ask a really, Some might say crazy question and I was really insecure about it afterwards and I called some friends and I called my parents and I talked to them and I was questioning whether I should have done it in the first place. And as I spoke to them about it, I actually rationalized it to myself and realized, well, this lady is talking with all of these really qualified candidates, I have to stand out. And if I don't get this opportunity, Because of what I said, that's a bummer, but I really don't think that I would be a fit for that environment if they don't want somebody who's willing to go out on a limb like that. I think that's a beautiful way to put it. I mean, what that brings up for me is you were intentional about what your goals were, you did what I call a litmus test question, which is depending on the answer for this, if they answer no, I don't want to work with them anyway. And so therefore the question has this magical kind of self qualifying nature. In that case, it's not necessarily asking a question or making a statement out of curiosity to know the answer. So much as it is about qualifying somebody. And again, back to consequences. If you don't care, if it goes wrong, then it really frees you up to be able to say and do things. that are meaningful. Now also say a coach I worked with and I've had a lot of professional help in learning this stuff. Like I learned the under the breath thing at McKinsey because they told you like the client often says the most important thing just as you're leaving the room, you know, and I had a coach who called what you just described a vulnerability hangover. So just because I don't care, ultimately, if a person dislikes me for doing something respectful, It doesn't mean. That I don't have a vulnerability hangover after I'll be like, I'll oftentimes call my business partners after a meeting or the person I was with. And it's like, was I really mean, just then, you know, because I'm worried, like, I don't want to be mean, but sometimes it can come off that way. I'm a New Yorker, you know, you know what it's like. And so just because I'm ultimately okay with it, doesn't mean I'm immediately okay with it. And the vulnerability hangover is real and something you have to manage. Just because you have a vulnerability hangover doesn't mean you did the wrong thing. I love that term. I'm going to start using that more often. And I'm also going to start managing my own more often. Sometimes you have a vulnerability hangover because it's trying to tell you, you did something you regret. And so I pay attention to those as data. It just doesn't necessarily mean you regret the thing. absolutely. And we'll see what happens with this opportunity and whether it paid off. But at this point, I think I've conquered that vulnerability hangover and now I'm just proud that I even tried it. So Awesome. I think that's great. That's such a Thanks. a muscle. You're building the muscle. That's the whole point of QuestionAble Strategy. That's what we're trying to teach people is asking better questions is a skill, not a talent and talking to people like you about how you develop the skill. That's going to help people who are trying to walk in your footsteps. So speaking of your footsteps, you currently lead Bloomberg Beta. You're a VC investor. And I think that a phrase that gets thrown around a lot by VCs is that they invest in founders. One of the reasons why you are here at all is because I really do get the impression from you more than any other VC that I've spoken to that you do care about founders. But what are you actually looking for when you talk about investing in founders? So I actually don't believe in The invest because of the founder thing it does happen But I usually think it's after the fact like after the fact is it obvious the founder was great Of course the company succeeded. It's usually obvious the founder was great I don't have the ability to like look into somebody's eyes or hear their voice and be like that's the one I just don't know like it's too many unconscious biases there too many looking for similarity if I do that What I do think is I know how to look for patterns where I don't want to work with somebody You Okay. Important. So like, if I think they're verbose, like I'm verbose enough, we don't need to verbose people. Um, But the other thing, and maybe I hope this is what came through is, we are religious as a firm about the founder being our customer. I have a lot of respect for founders. So even a founder who I don't know if they're that talented, I think their business is a stupid idea. I still really respect them because A, I might be wrong. I'm wrong a lot. If I weren't wrong a lot, I wouldn't need a portfolio of bets. And B, I think that the credit, it's like that Roosevelt thing about like the credit goes to the person in the arena. And so like, it's really easy for me to sit here and have a fucking opinion, but I'm not putting my life into that opinion. So I have a lot of respect for the fact that they are And it's not a friendship relationship, at least not at first. It can evolve over time into that. It's a respect for a potential customer who I admire. And the way I put it is imagine if I were like a doctor to athletes, you know, it's like, I admire the athletes. They can do things that I'm not doing or that I can't do. And so I think it's that respect. And sometimes I can cut both ways because sometimes people feel that I respect them, but they can also intuit that I think their idea is a dumb idea. And then it's even more painful. Because I'm not being dismissive of them. Like, I actually think their baby is ugly, but also, I don't know! Like, I can't tell. And I read this post a long time ago. It might have been Paul Graham, who I find in a lot of ways. But he sometimes says some wise stuff, and you gotta learn from people. probably going to listen to this Yeah, right, of course. Paul, hi. But he said something about how the person you meet, Who seems like a schlub might end up being the next wildly successful founder and I my conclusion from that is Therefore treat everybody like they might be wildly successful because you just don't know and it's a better way to treat people I mean, be nice to people is just a way to go about your life Again Nice. I struggle with because it's not like I'm being gentle. It's not like I'm being kind. I want to get at the truth and help them succeed. And I am selling from the very first moment in a very particular way. Because one of the things I experienced as a founder is you'd have the VCs would be like, Oh, like, I don't give a shit. I'm not interested. And then the business pops. And they're like, whatever happened to that meeting? And it's like, you're an inauthentic dipshit. Why would I want to work with an inauthentic dipshit? And so I'm selling from the first moment, even if I don't ultimately want to ask to invest. And my way of selling is by asking them the questions about how their business is. Cause if I were already working for them, that's what I'd be doing. One thing I've heard zero times in 11 years of doing this is, wow, you were totally different in the upfront investing process compared to the working together process. I wanted them to see what's on the tin so they can pick us if they want to work with us. I, I hear that. And I guess I'll amend my nice comment to Be respectful of people, and I think that's a lesson for life, that's right, but whatever they read as respect or what I read as respect might be different depending on a lot of personality, culture, like all kinds of stuff, but that's my intention. of course. In those initial meetings with founders, then what questions do you find elucidate a founder's tenacity and drive better than others. A question is not always the right way to get at something. So like, I'll look at their past experiences before I meet with the founder. I'm pretty sure I did this with you, Antonia, if I had it is I will go check out. Who I know, who knows them and I'll ask for the references that I trust before I talk to the founder the first time, because that's way more valuable than whatever my opinion is. And then I'll just listen to what they say. But like, you know, you can't ask somebody about tenacity. Like, Oh, what's an experience where you've been tenacious. It's like, I don't know, either. I'll struggle to search my memory or I'll give you some canned bullshit. You got to just observe I guess the lesson there to me is that an explicit question is only the right way to get at things some of the time. Other times there are other cues and clues that are more useful than an explicit question. I think that's really important to keep in mind, especially as people are listening to our episodes and reading our blogs. Just thinking about how to ask a question is half the battle. For instance, I believe that listening is the greatest chunk of asking a great question. Yeah. Yeah. I'm terrible at it by the way. Like I just say, I'm terrible at it because I, I'm a chronic interrupter, but I'm also terrible at it because part of listening is internalizing. Part of it is the theater of demonstrating to the other person you are listening. And oftentimes I'm listening, but it seems like I'm not. And my kids do this to me and it's maddening and I do it to other people. And I imagine it's maddening to them. I'll look around, I'm on my phone, but actually I'm listening. It's just how I do it, you know? And back to my former boss, Dan Doctoroff, he's often seen as a talker. And I actually think he's an incredible absorber of information. He would describe that as listening and I think sometimes it is But I think that other people didn't necessarily always believe he was listening In part because of cultural differences he's like a loud tall man, you know in part because of body language and all kinds of other things and in part because maybe sometimes he wasn't listening Are there methods that you may use since you're conscious of the fact that you might not be giving these visual cues of listening? Are there ways that you try and convince people that you have been listening? Great question I'm not sure, because I think if I were doing it intentionally, it would be theatrical and inauthentic, and I want to be authentic. I guess I'd just say, a practice I'm in the habit of, which I've learned mostly through like personal growth work and therapy and I used to do peer counseling when I was in grad school at a 24 hour, hotline is repeating back what you heard the person say. Is such an underused underused technique. It can be overused. At McKinsey, it's overused. What I'm hearing you say is, it's like, yeah, that's literally what I just fucking said. So you gotta, you know, there's some chemistry to it and some interpersonal nuance to it, but I'll often start a meeting and be like, I read your deck. Here's what I took from it. Please correct me. I'm not trying to say I know I'm trying to illustrate that I've read I'm trying to get my facts right and have them correct me and sometimes they will as opposed to like I read your deck and Now i'm going to sit back and let you recite it to me in a theatrical canned way I'm, just bored and the reality is i'm not always listening because sometimes people are boring Sometimes people say things that aren't worth listening to and I just want to be real about that. And sometimes they'll say something really worth listening to like I have a friend. She's maddening to me Because she will talk for five minutes and most of it I'm like, Oh my God, please stop. But then there's that one little thing. So I will pay attention for the whole five minutes and it's maddening. Cause it's like, take strain cause I'm bored, but then that one nugget makes it worth it. And so not treating a failure to listen as a moral failure in yourself, I think is part of it too I'm curious because you've mentioned that you're from New York and so am I, and you're also vocal on Twitter or what was formerly known as Twitter and now X, but what I find really interesting is the differences that you draw between New York and San Francisco or Silicon Valley more broadly, and I'm wondering if you see a kind of cultural difference within the tech ecosystem between New York And San Francisco, when it comes to their approach to asking questions and curiosity. Awesome question. They differ in many ways, deeply. I'm unsure if that's one of them. I honestly have to think about that more. I really don't know. I'm tempted to like kind of resort to quick stereotypes about what New Yorkers are like. And, and to be honest, I'm not sure if in my professional life I have seen a systematic difference. I mean I think everywhere you go people are more interested in themselves than in other people. And that's true in the Bay Area. And it's true in New York, everywhere you go, people go through the motions. You know, the worst offenders of this are LPs investors in VC firms and other investment firms, but investors in investment firms doing references. It's like such a box checking exercise. It feels like, you know, I'm going through like answering somebody's FBI background check questionnaire. I'm not sure how much those differ from place to place. I mean, I guess I'd say this people tend to ask questions about the things they know about. Because they just feel more comfortable. I'm sure I do it too. And the kinds of things people know about do tend to differ to some degree between the Bay Area and New York. I Mean, I think the stereotype is true that like your typical VC in the Bay area is probably slightly more technical, usually, not always, but usually kind of thing. That makes sense. Another comparison that I've seen you write about on social media is sort of this transition from older, more experienced VCs to new. Younger, more fresh faced VCs and it's difficult for those younger VCs to succeed. So do you think that there are key differences in the ways that these younger VCs express their curiosity and ask questions or what, what do you think that really comes down to? My first reaction I'm having is like, Oh, which one am I? I think I might be stuck in the middle. You're not doing it. I'm just. Commenting. I think I'm probably in the old category at this point. No. It's just fine. I'm not bothered by it. Most people early in their careers, and I think this is true For young investors too you know, I do this somewhat regular thing, "This Is Not Advice," which is at thisisnotadvice.org Love This Is Not Advice. Thank you. Big fan. Thank you. I think that the questions that people tend to ask earlier in their career, they tend to be copying questions they've heard other people ask, which is a totally appropriate way to do things. Like, that's how you learn. You copy some things and you see how it goes. Of course. We're all babies. Exactly. We're all babies. We're all babies indulging in the scientific method. The issue is that that doesn't reflect having done your own knowledge or having lived your own life. And so saying like, Oh, I experienced this thing. Therefore, I've got this question about what you're doing is a really valid thing to do. I mean, when we invested in Flexport, Flexport as a shipping broker I had been the co founder of a startup I mentioned earlier, and we had used a shipping broker. And so I had some experience with it and asked based on my personal experience. And I guess earlier in people's careers, they often either haven't had the wide range of experiences to use as the basis for questions, or they don't feel confident knowing which of their experiences are worth asking about. And so you tend to get these generic, repetitive questions. Sometimes they're literally have their boss asking them to ask questions, which is the worst It got to the point where with VC references for LPs, where I'd be like, here are the eight questions you were likely to ask me. Here are my answers to all of them. Do you still want to have a call? Somebody laughed about that. but it was because they were all such generic questions. Whereas I think as people go, if they focus on getting better at it, they'll develop their own repertoire. Of questions, Dan Doctoroff, for example, he has like a set of four standard interview questions. I was once in the interviewing group for a science fellowship. The Schmidt science fellowship that they do with Rhodes house and the Rhodes trust rather. And we all asked the same question in every interview. And some of the reasons for that is benchmarking. If I ask 10 people the same question, then I learn based on the differences in their answers. So not every question has to be bespoke. A lot of the questions we ask founders are the same. In fact, they're published on our website. And I do love that you do that. Bloomberg Beta is very transparent with the process and it gets those questions out of the way as well so that there's more room for more interesting, unique questions, I guess my point of bringing that up is that It took a while into my career before I converged on some standard questions that I wanted to ask. And then the other thing I just say is later in your career you need to ask fewer questions because you're getting a lot of it. Implicitly perceptual knowledge. Like I would like to think this would be a crazy experiment to run. Do you know that Nalini Ambady psychology experiments? When I studied psychology they shared this study with us, where at the end of a whole semester, students would fill in like a evaluation form about their professor rating the class. And so they just want to see how much exposure do you need. So they'd have students take just the first lecture and then do the form. And the results were like 99 percent correlated. They're like, huh, what if they only watch 10 minutes of the first lecture? Huh, what if they only watch it with no sound? Eventually it was six seconds black and white with no sound. You had a statistically significant correlation between the ratings of the class and after students had taken a class for a whole semester. And so some of me thinks that as you build more habit, like maybe I just need to sit with a founder for six seconds, black and white with no sound and come to my judgments about it. And part of that is because by the time we entered the meeting, we've actually already done a lot of work. And so that meeting is not as consequential as people think it is and the consequence for your podcast is therefore I need to ask fewer questions That's such a great takeaway because sometimes the strategy behind asking better questions is asking fewer questions. Saying more is not necessarily saying more important stuff. something. That you brought up very, very briefly is you were a Rhodes Scholar. How did being in that small prestigious community with young scholars that were studying very different disciplines influence your worldview? I I brought up that I was involved in interviewing, but I was a Rhodes scholar. I didn't I mean it wasn't my attempt to like He was a Rhodes Scholar, everybody. I you know Also as i've gotten older i'm like I I used to hide a bunch of those things And I hid them because if I shared them it would be sharing them out of insecurity in order to brag And now while I still may do that unconsciously it's all a little less loaded for me in part because it's like, yes, and I can buy a cup of coffee at Starbucks for the same price that everybody else can. And I just had a group of Rhodes scholars who are students now at my house last night for dinner. They're considering entrepreneurship. And we had like whole fireside chat thing. And I guess I'd say that is one of several communities of extraordinary people that I've been fortunate to be part of. Real talk. Not that much more or less extraordinary than many other communities. Like I think about the best students at my high school, kind of comparable, very comparable. In fact It's good to know, as somebody who isn't a Rhodes Scholar. You'll be fine. Actually the data I want are, I think Jimmy Carter was a finalist, but didn't get it. The data I want on everything is who the near misses were. I want to know the best company ever that got turned down from YC YC will often do analysis of who they admitted, but I want to see the analysis of who they didn't admit. I'd love to see that too. If YC is listening to this podcast, we want that. The people want it. Yeah, Garry, let's hear it. Again. That's the question. There's this Amazon line about like the dogs aren't barking, which I never fully understood, but it has something to do with the data you're not getting being the thing that tells you something. And so there is no such thing as a community where every person is extraordinary. A lot of them are comparable to each other, and I've tried to learn from all of them in different ways. I'm open to finding the extraordinary in many places, and I do feel fortunate to have been part of several extraordinary communities, including having been a Rhodes Scholar. Of course. A community that I would want to bring up because it's and dear to my life is the world of politics. That's where you got your start And I'm curious, bringing it back to questions, having spent time around politicians and founders, I can imagine that you've seen this common thread of, don't answer the question that you've been asked, answer the question that you want to answer, and I want to know from you, how do you get politicians and founders alike to actually answer what you're asking I think obviously all people are similar, but they are very different, and back to the Rhodes Scholar community, they've done great in politics, but like, the very best companies started by Rhodes Scholars? Not that great. All due respect to my Rhodes Scholar classmates and whatever, they're great, but they're not that great. It's not like of the top 10 companies. One of them was started by a Rhodes scholar. I don't think that's the case. I guess this gets back to what's normal and expected. And by normal, I don't mean like some subjective judgment. I just mean what adheres to norms, which is to say knowing what it means when a politician answers a question in a certain way is really different from knowing what it means when a founder answers a question in a certain way. And you only know that by asking lots of people lots of questions and seeing what their range is of how they respond. And I think politicians tend to respond in a much narrower range for a variety of reasons. And for me I'm also trying to be aware of those norms as an answerer. In the sense that I want sometimes to adhere to the norms, and I want sometimes to defy the norms, but I want to be intentional about when I do which one. I think lines up very well with my experience having been in the political world and in the tech startup world, I really like the way that you frame question asking as being a kind of scientific experiment over time, which plays very well into our mission and what it is that we're trying to do with QuestionAble Strategy, try it over and over and over again and you'll learn and you'll get better. I think that's a key takeaway. here. I think it's an amazing goal to have to encourage people to practice this more. One of the cool things about asking questions is unlike investing in startups. You get lots of opportunities every single day. And so this is a thing everybody ought to be able to be better at because everybody has opportunities to try all the time And it's low stakes too. You're doing this for yourself. Or you can control the stakes. You can ask a really difficult question that has high stakes, or you can go gingerly And that's okay. All of it is okay You do it in your own style. I think that's beautiful. My last question for you is what is one question that you like to work into a conversation, whether it's at work or even in a social setting that really helps you get to know someone? I wish I knew. I wish I had, that's what I would call a skeleton key. I don't have a skeleton key that can open any lock. I think that my method is less a question, is paying attention to what they're talking about and just being interested in that thing. Like I could talk to somebody endlessly about a thing that they are interested in, and usually that is what will get people to open up. It's hard for me, not everybody. And, you know, I'll give you one that sometimes works for me. Once I know somebody a bit, it's a little bit of like uh, that's a weird question. But one that works for me is I ask somebody where their resting mind is going. Because our resting mind often gravitates to the thing that we are preoccupied with. I think it's important for a standard question to be slightly different because otherwise people don't think about it. I'll tell you the hardest question for me to answer. This is going to sound bizarre is when somebody says, how are you? Like, I don't know. You want to hear like. About like all the life that led me to this point what i'm thinking about right now You want me to bullshit you and say fine, How much time you got? Right. I get tripped up on what is the purpose of that interaction? And if the purpose of it is just nonsense filler I struggle with that purpose because like while I disagree with Elon on many things one place I agree with him is I think small talk should be illegal That's a fantastic note to end on. Roy, this has been wonderful. Thank you so much for coming on to QuestionAble Strategy. I thoroughly, thoroughly enjoyed this conversation. And like I said, it's been three years in the making. I've wanted to ask you a lot of this stuff. So this is truly a pleasure. Keep asking me more questions i'm grateful you're doing this and I'm grateful to be here I really enjoyed that conversation. Like I said, I was waiting three years to chat with Roy about the questions that he asked me. When I say that I've spoken with hundreds of VCs and very few of them actually ask any questions that are unique or that stand out or that make me feel like I'm any different from just the other thousand founders they're talking to. I actually really mean it. So, in the spirit of QuestionAble Strategy, I'm here to learn, too, and I'm here to get better at questions. That's why I started this podcast in the first place. So, I asked Roy at the end of our conversation if there is a question that he likes to ask to get to know people better. He said that sometimes he likes to ask people where their resting minds go to. And I really took this to heart. It got me thinking, That's definitely an odd question. It stands out. It's not a question that I've ever been asked, but I think, fundamentally, what it is is a different way of asking. What's on your mind? What's bothering you? My first impression of that question is that it was an opportunity to complain Maybe that says something about me, but that was my first impression. So I resolved to go out and ask some friends in a social setting where their resting minds go One thing that I will say about this question is that it was actually kind of difficult to weave into a conversation. There were several social engagements that I went to where I thought going in, Oh, this might be an opportunity to pull out the question and get people's responses so that I can talk about it on QuestionAble Strategy. But many of those social engagements came and went without a proper window for me to ask that question. So that's my first impression. But The opportunity came up a couple of days ago when I was hosting a friend, Jack, over for dinner with my flatmate, Anna, at our flat. And I cooked some dinner for everybody. We sat down, we ate together, and I'll just say that I felt really comfortable in that situation because I knew both of them are particularly deep thinkers. We're also pretty close, so it's not like we're strangers. Anna and I live together. Jack went to college with us. And so we've known each other for a really long time. That's important to note because it just means that we have a pre existing close relationship. And I also mentioned that they're both Deep thinkers. So, I trust that they're both introspective. It's not like we're sitting around having solely surface level conversations and then all of a sudden I pull out this really deep where does your resting mind go question and catch everybody off guard. Still, though, Where Does Your Resting Mind Go? is not an easy one to weave into a chill, friendly, happy discussion. Especially because, in my mind, I was expecting people to talk about what was stressing them out. Therefore, when I finally got up the courage to ask this question and insert it into the conversation, I kind of did it in a really clunky way. I stopped the conversation and I said, Hey guys, do you mind if I ask you a question? And perhaps I even said, Hey guys, do you mind if I ask you a kind of random question? So I was already creating this cushion around myself because I felt not embarrassed by the question, but I just knew that it was taking our conversation to a deeper level than where it had been beforehand. And so I said, I'm going to ask you a random question. Where does your resting mind go? And both of them seemed a little bit shocked by the question. They didn't seem offended by it, and they didn't seem weirded out by it. They just weren't expecting it. And they both took a couple of seconds to think to themselves. It was quiet for a little while, and I was fine with that. I knew that it was probably something that they needed to think about. And Anna was the first one to speak, and she misunderstood the question a little bit because she said, well, I think that it's when I'm not thinking about anything. And I said, okay, well, can you say more about that? What do you mean? And she was like, well, work is so chaotic. That the only time I get to relax is when I really feel like my mind is just empty, and I realized then and there that I needed to clarify: Your resting mind doesn't mean your relaxing mind. Your resting mind is just where your mind drifts off to. Something that's bubbling underneath the surface and that comes up when you don't have Slack messages popping up or WhatsApp messages or emails to respond to. It doesn't necessarily mean that you're relaxing and chilling out and in a zen place. It could, but it doesn't necessarily mean that. And so, then, once I clarified that, Anna said, Oh, well it's definitely all the work that I have to do that's outside of what I do for my job. Anna is preparing to take some exams, and she said that she gets really preoccupied. With that kind of daunting task that's looming over her. Moving on to Jack though. His answer really surprised me because he said oh Honestly, as of, as of late, it's been Dune and I was like, okay, you know, tell me, tell me more. What do you mean? And he was like, well, you know, did you see Dune Part Two? And I said, yeah, of course I did. I loved it. He said, when I'm sitting and don't have much else to think about, I just catch my mind drifting to Dune. It's not something that I can control. I just, Run through plot points and symbolism and character development from Dune, and then I'll I'll snap out of it and realize that that's what I was just thinking about, or I'll come to some realization about a connection that I hadn't seen before. He also said that recently he's been thinking about the Three Body Problem, which is another sci fi book that's been turned into a series on Netflix. This answer was so fascinating to me because it broke the mold of what I expected. It went against my hypothesis, which was, oh, this question is an opportunity for people to rant about what's going on in their lives and what's stressing them out. And instead, Jack's resting mind thinks about sci fi concepts and tries to find connections in stories. And I thought that that was really nice. I thought that sounded incredibly entertaining. I think that's a worthwhile way to spend your time, even if it's inadvertent. Um, and so I really appreciated his answer. And from both Anna's answer and Jack's answer, we got into deeper conversations about stress and about upcoming tasks. But also, we got to talking about the value of sci fi when it comes to reflecting on the way that we live in our society and the way that we approach stories and also got some good recommendations for TV shows that we should watch on Netflix. so it was a great way ultimately to open up a deeper conversation on multiple levels. What I will say though, is that. This is definitely a question where you need to be prepared for it to get flipped on you. Because if you bring up a question this weird in conversation, you better have an answer And so when it got flipped on me, I definitely took it in the sort of stress way. Because I have a lot of transitions and changes going on And so I just find myself stressing out about what decisions I'm supposed to be making and if I'm making the right choices. But then as I thought about it a bit more, I realized, oh, actually another place where my resting mind goes is I tend to think about my siblings a lot. When I don't have anything to think about, I honestly like I'm going to entertain myself by thinking about my brother and my sister's lives, because they're so different from mine. And even though they're younger than I am, I really admire them. I find the way that they think, and their interests to be really fascinating, not necessarily because I know anything about those topics, but because I just think that they're amazing people, So overall what I would say is I really like this question because it forced me to reflect. I also asked it to two friends who would definitely appreciate the question take it seriously. Nobody thought of it as a joke. Nobody got disrespectful. Everybody was taking it seriously. It's really interesting to hear what everyone else had to say, but it's difficult to work into a conversation and there are probably better ways to get a similar result. I need to think about it a little bit more. It's definitely worth trying if you feel like you're in a comfortable enough place with people that you know well enough. I probably wouldn't ask this question to strangers at all. I'm glad that I did it with people who. I know already. it's a great way to get to know somebody better. So it does definitely answer the question that I asked. So thanks Roy, but it comes with its challenges for sure.
